JPS6245577A - 1-arylpyrazole - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel 1-7 lylvirazole, its production method, and its use as a pest control agent.
It particularly relates to use as insecticides and acaricides.

Certain pyrazole derivatives, such as 1-cyclohexyl-5-(N,N-(dimethyl)-carpamyloxy)
-3-Methylthiomethylpyrazole or 1-cyclohexyl-5-[N,N-(dimethyl)-carbamyloxyJ-3-methylsulfonylmethylpyrazole has insecticidal, nematicidal (ne@atocidal) action and bactericidal action. - It is already known that it has fungieidal action.

However, the level of action and duration of action of these compounds are not always completely satisfactory in all fields of use, especially against certain insects or when used at low concentrations.

General formula (1) where R' represents hydrogen, alkyl or halogenoalkyl, R2 is furkyl, halogenoalkyl or aralkyl which may be substituted in any case or 7
a novel 1-7 lylvirazole, R3 represents hydrogen or halogen, Ar represents optionally substituted phenyl or pyridyl, and n represents a number of 0, 1 or 2; discovered.

Furthermore, the general formula (]) in which R1 represents hydrogen, alkyl or halogenoalkyl, R2 represents alkyl, halogenoalkyl or aralkyl or aryl which may be substituted in each case, and R3 represents hydrogen or halogen , Ar represents optionally substituted phenyl or pyrinol, and n represents a number of 0.1 or 2. A novel 1-7 lylvirazole of the formula (n)^r in which R1, 5- where R2, A' and n have the above meanings;
7mi/-1-7 lylvirazole with an inorganic nitrite or an organic nitrite ester in the presence of a reaction aid, optionally in the presence of hydrohalic acid, and optionally in the presence of a diluent. It has also been found that it can be obtained by the reaction method described below.

Finally, it has been found that the novel 1-7 lylvirazole of general formula (I) has insecticidal and acaricidal properties.

Surprisingly, 1-7 of general formula (I) according to the present invention
Reelvirazole is a bifusol derivative known from the prior art, which is a closely related compound both chemically and from the point of view of action, such as 1-cyclohexyl-5-[N
, N-(dimethyl)-carbamyloxy]-3-methylthiomethylpyrazole or 1-cyclohexyl-5-
It exhibits better insecticidal and acaricidal activity than (N,N-(tumethyl)-carbamyloxy]-3-methylsulfonylmethylpyrazole.

Formula (1) gives a general definition of the 1-7 lylvirazoles according to the invention. Preferred compounds of formula (1) are those in which R1 represents hydrogen or has 1 to 4 carbon atoms; represents alkyl or halogenoalkyl, in each case linear or branched, having from 1 to 9 identical or different halogen atoms, where R2 is in each case 61 represents an alkyl or halogenoalkyl having from 1 to 8 carbon atoms and, where appropriate, from 1 to 17 identical or different halogen atoms, which may in each case be straight-chain or branched; or, as appropriate, having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety and in each case mono- or polysubstituted by the same or different substituents. 722furkyl or phenyl, in which the possible substituents on the phenyl are in each case: halogen, cyano, nido a and, in each case, on the individual alkyl moieties. Alkyl, alkoxy, alkylthio, alkyl, in each case straight-chain or branched, having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms Sulfinyl, alkylsulfonyl, halogenoalkyl,
Halodephalkoxy, halo5/alkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl, R3 represents hydrogen, fluorine, chlorine, bromine or iodine, and A' is phenyl, 2-pyridyl, which may be substituted or polysubstituted;
3-pyridyl or 4-pyridyl, in each case with possible substituents; cyano, nitro, halogen, in each case with 1 to 4 carbon atoms, in each case straight chain Alkyl, alkoxy and alkoxycarbonyl, which may be branched or branched, and in each case 1 to 4 carbon atoms and 1 to 9
halogenoalkyl or halodephalkoxy, which in each case may be straight-chain or branched, with identical or different halogen atoms, as well as groups! 3 (O)m R' (in this formula, R4 represents amino, or in each case alkyl, which may be linear or branched, flukylamino, diflukylamino or halo5//alkyl) and in each case each alkylthio has 1 to 4 carbon atoms, and in the case of halogenoalkyl, 1 to 9 halogen atoms, the same or different. The digit represents the number 0.1 or 2), and the mouth represents the number 0.1 or 2.

Particularly preferred 1-7ylvirazoles of formula (I) are those in which R1 represents hydrogen, methyl, ethyl, n-likely i-propyl or trifluoromethyl, and R2 represents methyl, ethyl, n- or i- propyl, n
-1i-, s- or t-butyl, n-! , L< is i
-pentyl, n- or i-hexyl, chloromethyl, difluoromethyl, difluorochloromethyl, fluoro aa aa methyl, tri-1,1 fluoromethyl, pentafluoroethyl, pentachloroethyl, fluorotetrachloroethyl, difluorotrichloroethyl, tri represents fluorodichloroethyl, tetrafluorochloroethyl, heptafluoropropyl, chloroethyl, bromoethyl, chloropropyl or bromopropyl or is in each case mono-, di- or trisubstituted by the same or different substituents Sometimes phenyl, pencil or phenethyl, possible substituents on phenyl are: fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, trifluoromethyl, methylsulfinyl, methylsulfonyl, Trifluoromethoxy! , 1 fluoromethylthio, trifluoromethylsulfonyl, or trifluoromethylsulfonyl, R3 represents hydrogen, fluorine, chlorine, or bromine, and Ar is 1, 2, 1, 2, or 4 with the same or different substituents. or 2-pyrinol or 4-, which may be mono-, di-, king- or tetrasubstituted, in each case by the same or different substituents; represents pyridyl, in each case with possible substitutions on phenyl or pyridyl: cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and C/i-propyl, n-1i-, s - and t-butyl, methoxy, ethoxy, ethoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl, tetoffluoroethyl, trifluorochloro mini chill,
Trifluoromethyl, difluorodichloroethyl, triple oronochloroethyl, pentachloroethyl, triJ
Fluoromethoxy, trichloromethoxy, dichloroe+fluoromethoxy, difluorochloromethquine, rialomethoxy, dichloromethoxy, difluoromethoxy, pentafluoroethoxy, tetrafluoroethquine, trifluorochloroethoxy, tripleoethoxy, nofluorocycloethoxy ethoxy, trifluorochloroethoxy,
pentachloroethoxy and the group -8(O)m R' (in this formula R4 is 7mino, methylamino, ethylamino, trimethyl7mino, diethylamino, fluorodichloromethyl, difluorochloromethyl, tetoffluoroethyl, toIJ
represents fluorochloroethyl, trifluoromethyl, methyl or ethyl, and n represents the number 0, 1 or 2), such that n represents the number Oll or 2.

The 1-7 lyl pyrazole of the following general formula (1) is manufactured by 31!
In addition to the compounds mentioned in the examples, mention may be made in particular.

^r 81 82 Rri ^
j”-1II ell・Br Oyop
F -C1' 11 CH•CI Oξ>, CI' For example, 5-7-7-4-dichlorofluoromethylsulfenyl-1-(2,6-cyclo4-trifluoromethylphenyl)-virazole is used as the starting material,
If 17um/hydrobromic acid (nitrous acid) is used as the reactant, the course of the reaction in the process described in the present invention can be represented by the following equation.

Formula (n) gives a general definition of the 5-amino-1-arylpyrazoles required as starting materials for carrying out the process according to the invention. In this formula (II), R'%R
2, Ar and n preferably represent the groups already mentioned as preferred in connection with the description of the substances of formula (1) according to the invention, considering these substituents and indexes.

The 5-ami7-1-arylpyrazole of formula (II) is a substance that is not yet known. However, these compounds are based on the West German patent application filed by the applicant company *P3, 40.
No. 2,308 and (No. 73-517,843).

These compounds have the general formula (III) 8r where R1 and Ar are 4-thiocyanato-5-ami7virazole or 2(■) where R' and Ar are as defined above. (Pyrazolyl) disulfide with the formula (V)R”-H
al' (V) in which R2 has the abovementioned meaning, Hat' represents a halogen, in particular a halide of chlorine, bromine or iodine, optionally in the presence of a diluent such as methanol or ethanol, and The reaction is carried out at a temperature of from 20°C to 90°C, optionally in the presence of a reducing agent, such as sodium hydroxide or sodium notothionite, and optionally a base, such as sodium hydroxide or sodium carbonate. , or formula (VI) 8, where R' and V Ar have the above meanings,
5-aminopyrazole with the formula (■)R2-3-)(al”
(■) In the formula R2 has the following meanings, HaN is a sulfenyl halide representing a halogen, in particular chlorine, hydrogen or iodine, optionally in the presence of a diluent such as methylene chloride. , optionally in the presence of an acid binder such as pyridine, at a temperature between 0"C and 50C, and then reacting the thus obtained formula (I[a) Ar, where R', R" and Ar are as defined above. on the sulfur of the sulfenyl group at the 4-position of the pyrazole ring, with the formula (■) R-0-OH (■), where R represents hydrogen, or , in each case optionally substituted alk/yl or aroyl, preferably hydrogen, or acetyl, or propionyl, or tri7fluoroacetyl, or substituted of a catalyst, such as ammonium molybdate, optionally in the presence of a diluent, such as methylene chloride, using an oxidizing agent representing benzoyl, such as 3-chlorobenzoyl or 4-nitrobenzoyl, optionally in the presence of a diluent, such as methylene chloride. and optionally in the presence of an acid binder, such as sodium carbonate or sodium bicarbonate,
It can be obtained by a method of oxidation at a temperature of 0°C to 50°C.

4-Thiocyanato-5-7 minovirazole of formula (III) is in some cases a known substance (e.g. 7 Farmaco Ed, Sci.
, > 38.274-382 [1983]), these are, for example, 4-unsubstituted 5-ami7virazole of the formula (1 in which R1 and Ar have the above meanings) with ammonium thiocyanate and bromine and acetic acid at a temperature of -20'C to +20°C.

Bis-(pyrazole) disulfide of formula (■) is a substance that is not yet known. These are 4 of the above formula (III)
-thiocyanato-5-7 minovirazole, optionally in the presence of a diluent such as ethanol, at 20 to 120°C.
It is obtained by a method of reaction with aqueous hydrochloric acid at a temperature of C.

The halide of formula (V) is a well-known compound in autochemistry.5 The 4-unsubstituted-5-aminopyrazole of formula ('/I) is
1 in some cases! It is a known substance (for example, Organic Chemistry Journal (J, Org, Cbem, 36 +2972
-2974 [19711 or Journal of Heterocyclic Chemistry (J, H
eterocyelie Chemistry)7,
345-349 (19701; see Oori Chemical Abstracts (C, A,) L: 13137e).

These are, for example, an arylhydrazine of the formula (IX) Ar -N H-N H2 (IX) in which Ar has the above meaning, first, in the PIS 1 step, an aryl hydrazine of the formula (X) in which R1 has the above meaning and Rs represents hydrogen or alkoxycarbonyl, and A represents herodene, hydroxyl, alkoxy, amino or dialkylamino, optionally in the presence of a diluent such as ethanol or glacial acetic acid, and The reaction is carried out at a temperature of -20° C. to +20° C. in the presence of an appropriate reaction aid, such as sodium acetate, to give a 7-lylhydrophonone derivative of the formula in which Ar, R' and R5 have the meanings given above. is cyclized in a second step at a temperature of +50°C to +150°C, optionally in the presence of a diluent, such as ethylene glycol ether, or
Alternatively, the intermediate of formula (XI) can be directly cyclized in one reaction step at temperatures between +50° C. and +150° C., optionally in the presence of a diluent, such as ethylene glycol monomethyl ether, without isolating the intermediate of formula (XI) in an intermediate step. When R', R' and Ar have the above meanings, and Rs represents alkoxycarbonyl, the compound of formula (■a) can be directly converted to in the presence of a diluent, such as ethanol or isopropyl alcohol, and if appropriate a catalyst,
For example, it can be obtained by a method of hydrolytic tanalysis and decarboxylation at a temperature of 50° C. to 150° C. in the presence of hydrobromic acid.

The 7-arylhydrofusine of formula (IX) is a known substance (for example, U.S. Patent Specification No. 4,127,575; U.S. Patent Specification No. 3,609,158; , No. 558, 399; Journal of the Oori Chemistry Society (J, Chem, Soc, ) C, 1971.

167-174) or by a simple analogical method (see 7-Penn-Weyl
Houben-Weyl)' Methods of Organic Chemistry (Meth
C
hemie)” volume χ929203 page, Chi7 Publishing (
1967).

7-crylonitrile derivatives of formula (X) are well-known compounds in organic chemistry.

Sulfenyl halides of formula (■) are well-known compounds in organic chemistry.

The oxidizing agent of formula (■) is likewise a well-known compound in organic chemistry.

Possible diluents when carrying out the process according to the invention are generally all solvents customary for noazotization reactions of this type. Suitably used solvents are, for example, halogenated hydrocarbons, such as chloroform or bromoform, or aqueous acids, such as hydrohalic acid or sulfuric acid, the acid component being at the same time V as reagent and/or reaction auxiliary.
1 function.

If bromoform is used as diluent, the corresponding 5-bromopyrazole is generally obtained, with bromoform functioning simultaneously as diluent and reagent.

The corresponding reaction in the presence of chloroform as a diluent generally involves a 5-chloropyrazole compound of formula (1) and a reduced compound of formula (1) having a hydrogen group at the 5-position of the pyrazole ring. give a mixture of This mixture can be separated by distillation.

The process according to the invention is carried out in the presence of an inorganic nitrite or an organic nitrite. Possible nitrites and esters are all nitrite compounds customary for noazotization reactions of this type. Particularly preferably used nitrites, esters are alkali metal nitrites such as sodium nitrite or alkyl nitrites such as t-butyl nitrite.

The process according to the invention is suitably carried out in the presence of a hydrohalic acid. In this case, 1-7 lylvirazole of the formula (1), in which the group R3 represents a halogen group corresponding to the 7-ion of the hydrohalic acid used, is obtained as a reaction product. In either case, an aqueous solution of hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid is preferably used.

The process according to the invention is usually carried out in the presence of reaction aids. Possible reaction auxiliaries are, in particular, strongly acids, such as sulfuric acid, phosphoric acid, or the abovementioned hydrohalic acids, in which case these auxiliaries act simultaneously as reagents and as catalysts. .

The production method described in the present invention can be carried out as appropriate in the presence of a suitable reducing agent. In this case, a 1-7 lylvirazole of the formula (1) in which the group R3 represents hydrogen is obtained as a reaction product. The reducing agent particularly preferably used in this case is hypophosphorous acid (83PO2).

In carrying out the process according to the invention, the reaction temperature can be varied over a considerable range6.
at a temperature between 120°C and +60°C, preferably between -20°C and +4°C.
It is carried out at a temperature of 0°C.

When carrying out the method according to the invention, 5- of formula (II)
7minor per mole of 1-arylpyrazole generally 1.0 to 1.8 moles of nitrite, ester, optionally 1
．． 0 to 20.0 moles, preferably 1.0 to 10.0 moles.
0 mol of hydrohalic acid, optionally 1.0 to 50.0
moles, preferably from 1.0 to 20.0 moles of reducing agent,
and optionally 1.0 to 20.0 mol, preferably 1
．． 0 to 10.0 mol of mineral acid used as reaction aid is used.

Nitrite and ester are usually dissolved in small amounts in an appropriate diluent to form 5-7/-1-7 of formula (II).
Add to the reaction mixture consisting of lilyvirazole, mineral acid, diluent and hydrohalic acid or reducing agent.

The reaction product of formula (1) can be prepared by conventional methods, e.g.
The crystalline product is worked up and isolated by furnace separation or extraction with a suitable organic solvent.

Identification is by melting point or proton nuclear magnetic resonance spectrum.

Alternatively, compounds of the formula (In) 8r according to the invention, in which R2 and A' have the abovementioned meanings, and p has the number 1 or 2, can be represented by the formula (1b) according to the invention: r from compounds in which R2 and A" have the above meanings,
The sulfur of the sulfenyl group at the 4-position of the pyrazole ring is expressed by the formula (■
) D<-0-OH (~1) in which R represents hydrogen, or R represents any jL5 optionally substituted alkafyl or aroyl, in particular hydrogen, or represents acetyl, propionyl or trifluoroacetyl,
Benzoyl which may also be substituted, e.g.
- using an oxidizing agent representing chlorobenzoyl or 4-chlorobenzoyl, optionally in the presence of a diluent, such as methylene chloride, and optionally a catalyst, such as ammonium molybdate, and It is obtained by oxidation at temperatures from 0° C. to 50° C., if appropriate in the presence of an acid binder, such as sodium carbonate or sodium bicarbonate (see also Preparation Examples).

The active compounds are well tolerated by plants and their toxicity to warm-blooded animals remains at a reasonable level, so that they can be used by harmful animals in agriculture, in forestry, in the protection of stored products and raw materials, and in the sanitary area. , especially suitable for controlling insects, pods and [7#; The active compounds are normally active against both susceptible and resistant species and against all or several stages of growth.

The pests mentioned above include: members of the order Isopoda, such as Oniscuq asellus, Armadillidium vulgare.
), and Borsellio scaba (Poreello
5cabar): Diplopoda (D 1plopocja)
those of Blaniurus gutulatus (Bla
niulus guttulatus); of the order Chilopoda, e.g. Geophylus guttulatus);
arpophagus) and S cuti
gera spp,): Symphyllales (SyIII
phyla), such as Scutigerella immaculata (S cutigerella immaculata).
); those of the order ThySanura, such as LepiSma 5acchar;
ina); members of the order Collembola, such as Onychiu almatus.
rus armatus); Orthoptera
era), such as Pla'79 Orientalis (
Blatta orientalis), American cockroach (P eriplaneta american)
a), Leuco7aea maderae (L eueopha)
ea maderae), German cockroach (B
1attella Brmanica), Anata
domesticus (act+eta doaiesti)
Gryllotalpa spp.
), Locusta a+igr
aLoria m1Hratorioides), Melanobulus di7elenchialis (Melanoplu
3differentialis) and cyst cell n-
Blurring rear (Schistocerca 1greF
iaria);
), such as Horphiicula auricularia (F
orf icu 1 auricularia); those of the order Termite (Isoptera), such as Reticulitermes (Reticulitermes);
spp, of the order A noplura,
For example, Phylloxera hastalix
ra vastatrix), penfigus (P e
mphigus 9pp. ), human lice (Pedi)
culuShumanus corporis), chemo/lice (Haematopinu9spp, ) and woolly louse (L 1noHnathuS sp.
p, ): Hajiramiro (ki4 al lophag)
a), such as Trichod
ectes gpp, ) and Damal
i-mouth ea spp, ); Thripidae (T h
ysanoptera), such as ercinothrips femora
lis) and thrips (Thrip9tabac)
i); Heteroptera, such as Eurygaster spp.
), Nosderk X-Intermegitus (D ysd
ercus intermedius), Biesma
Quadrata (Piesma quadrata),
Bedbug (Cimex 1ecLularius)
), Rhodnius prolix (Rhodnius p.
rolixuS) and Doria) v (Triajoma
91)11. ); Homoptera
a), for example Alephrodes 8 Brass Crabs (A 1
eurocjes braqsicae), Bemisia tabaci, Trialeurode
s vaporariorun), cotton s vaporariorun (
Aphis gossypii), radish aphid (B revieorync braqsicae)
), CryptoBzus ψribis
ribis), Doralis・7az<-T-(Dora
lis fabae), Doralis Bomi (Doral
is pomi), apple boll beetle (E rioSo
wa lanigerum), peach aphid (Hyalopteru Sarundinis), and wheat aphid (M acrosiphum aphid).
vcnae), Myzus spp.
), hop aphid (Phor.), hop aphid (Phor.

Jon huIIlu l i), wheat aphid (Rhopaloqiphum padi),
Empoasca spp.%Euseelis bil
obatuS), black leafhopper (N ephote)
ttix cincticepS), Cornus cincticep (Lecaniua coni), Olive cincticep (S aissetia ole)
ae), brown-bottomed planthopper (L aodelphax
5 triatel 1 us), brown planthopper (N 1
Aonidiella aurantii), Aonidiella aurantii
), A 5pidiotush
ederae), Pseudococcus (Pseudococcus)
oceus spp, ) and Kijifumi (Psyl
la spp, ); Lepidoptera
tera), such as 7rihu>worms (Pect).
inophora gossypiel! a), Bupaluq piniar
ius), Cheia+at
obia brua+ata), Lysocholetis plancaldera (I-1thoeolletisblanc)
ardella), Hypo/Myutaφbapra (Hypo
nomeuta padella), Crucian carp 7y (Pl
utella maculipennis), Japanese plum beetle (Malacosoma neustria),
Mulberry/king bug (Euproctis cbryq)
orrhoea), gypsy moth (LyIIlant,
ria spp, ), Hucculatrix sulberinib (Hucculatrix Lhurberi)
el Ia), Citrus leafminer (PI+yllo)
cni3tis citrella)・ya7y(A
grotis spp, ), Euxo
aspp, ), 7 FelLia spp.
, ), Near Insulana (Earias 1
nsulana), Heliothis (to)
spp, ), heroic mojotu (+-aphy
gma exigua), armyworm (M ame!
! Panolis flaa++nea, Spodoptera spp., Spodoptera spp.
Trichoplu3ia
ni), Carbocapsa bomonella (Carpocaps
7pomonella), green caterpillar (P 1eri!3)
spp.

), Pyrauqta nubiliS (Chils spp.), Pyrauqta nubiliS
), Sunoko Namaguramei ff (Ephestia k
uehniella), honey fu' (Gallcr
ia mellonella), Tin'eola bisselliella
), Finea+ /<Lionella ('Finea pe
Iofmannophila pscu
dospreLella), Cafecia φ Bogna (Ca
coecia podana), Capua reticulana, Choristoneura @7mi7erana
fumiferana), Crysia ambiguera (
Clysia ambiguella), Homona magnanima, and Tortrix viridan
a): Coleoptera, such as A nobiu@punc
tatum), Rhizope
rtha cloIOinica), Purcinous
B rucbidius obtec
tu・Shun, kidney bean weevil (A canLI+o
seelidesobtcctus), Hylotorves
Hylotrupes bajulus
), Agela3tica
alni), Lep 17 Tarsa Desemlineata (Le
ptinotar3a decemlineaLa)
, 7 aedon 0 Cochleariae (P l+aedon
coehleariae), Diabrotica (D 1ab
rotica spp. ), Psylliodes chryso
cephala), E pi
lacb++a varivestis), Atomaria (Δtomaria 9pI1.), /Oryzaephilus qurinaa
+cnsis), Anthonomu
s Spp, ), Sit.

pbilus Mpp, ), Otiorrhychus 5ulcatu
s), the cabbage weevil (C.

s++opolit, es 5ordidus), Ceuthorrhyn
chus assiIIIillis), Hypera poqLica, Dermestes spp., Trogodel? (Trogodcrma 81111.),
Anthrenus (A nLhrenus 311111
．． ), Attagenus spp.
), yctus 9911
．． ), Meligetes Aeneus (Meliget,
hes aeneus), leopard beetle (P ti
nil! ! ! 'Jpp, ), Niptus hololeucus (N+[+Lu5hololeucu3), Gibbiuipsylloides
), Tribol iu+o species, Te+u:bri.

wolit (+r), click beetle (A Hrioje
s qOp, ), Conoderus
9p1), ), Melolongsa meoguchi (Mel
olontha melolontha), Amphi+mallon
Sol! Htitialis) and Costeritra
Costelytra zeala
ndiea); Hymenoptera 7, for example v ”7 /% / (D 1pri
on spp, ), Hoploca
mpa spp, ), L asius
spp, ), Monomorium
pbaraonis) and wasps (Vespa
spp, L Diptera (D 1ptera), such as Aedes
edes spp, ), A noph
eles spp, ), Culex s
pp, ), Drosoph melanogaster
ila melanogaster), house fly (M
usea) species, F annia sp.
p, ), Callip
hora erythrocep1+n1a), Lueilia spp, ), Chrysomyia spp, ), Cuterebra!!111, ), Gastrophilus spp, yppobosca spp, ), stable fly (S to+noxys spp, ) , Oestrus spp.
(Hypodere+a spp, ), Ab (T
abanusspp, Tania
spp, ), B 1bio hortu
lanus), Oscinell 7 litho (Oscinell)
a frit), P horbia
spp, ), P ego@
yia hyoscyaw+i), Ceratitis capiLata
, D acus oleae and T 1pula palud.
osa): of the order Chiliformes (S 1phonapLera), such as the Xenopsyl flea (X enopsyl
It eheopis) and Cerat
opyllus spp, ); Komagata JJq (A
rachnida), e.g., t +r X -t
Ruhio'v urus (S corpio mauru)
s) and Latrodectus mactans (L atrod
eetus maetans); and Acariformes (A c
Arina), such as Aciptoconagni (A c
arus 5iro), Himeguni (A rgas
spp, ), Ornithodoros
spp, ), red mites (Dere+anyssus
gallinae), Eliof Jesus Ribis (E.
rioplies ribis), citrus rust mite (Phyllocoptru La oleivor)
a) Boophilus spp.
, Rhipicephalus sp.
p, ), 7 amplyomas (A mblyomma s)
pp, ), Hyaloa+ms sp
p, ), Magni (I xodes spp, ),
P5oroptes 91
)11. )% Choriop
tes spp, ), S. areopt.
es spp, ), dust mites (7arsone+
*us spp, ), clover hagni (B ryo
The active compounds according to the invention are not only used against plant pests, sanitary pests and stored product pests, but also against plant pests, sanitary pests and stored product pests. In the field of veterinary medicine, parasites (ectoparasites), such as scale ticks and mites,
her tick), hunting mite (hunti)
ng 5ite), chiber, flies (stable flies and name flies), parasitic fly larvae, lice, woolly lice, stone lice (leather 1ice)
) and fleas.

The active compounds are active against normally susceptible species and varieties as well as against normally resistant species and species, and are active against all ectoparasitic, parasitic and non-parasitic species. active against growth stages.

The active compounds according to the invention are characterized by strong insecticidal and acaricidal activity. These are insects that damage plants, such as mustard beetles.
beetle(PI+aedon cochlear
iae)) and mites that cause damage to plants, such as the two-spotted spider mite (Tetranychu).
s urticae) with particularly good results. In addition, the active compounds are also suitable, inter alia, for controlling soil insects and can be used, for example, for controlling phorbia anitqua maggots.

The active compounds according to the invention also have a strong action against sanitary pests and pests of stored products, for example against the house fly (Musca domesticus).
For the control of a), weevils (comiIIon c.
orn weevil(S 1tophilus
granarius) or Madeira cockroach (L.
euCophaea maderae)). Furthermore, the active compounds according to the invention can be used for the control of pests of warm-blooded animals that live as parasites, for example against the larvae of the golden fly (Lucilia cuprina) or against the stable fly (S to
calcitrans) with particularly good results. The active compounds according to the invention also have good fungicidal and acaricidal activity when used in corresponding amounts and can be used, for example, for controlling Botrytis species and Venturia species.

The active compounds can be prepared in conventional formulations, e.g. solutions, emulsions,
Suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compounds, microcapsules in polymeric substances and in seed coating compositions, and also in combustion devices and tigers. It can be converted into formulations for use, such as fumigation cartridges, fumigation cans, fumigation coils, etc., as well as ULV cold mist and warm mist formulations.

These formulations are prepared in a known manner, for example by combining the compounds with fillers, i.e. liquid solvents, pressurized liquids, and/or solid carriers, optionally with surfactants, i.e. emulsifiers and/or dispersants. Obtained by mixing with a foaming agent.

If water is used as extender, organic solvents can also be used as auxiliary solvents, for example.

Principal suitable liquid solvents include: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes; chlorine-substituted aromatic or chlorine-substituted aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride; cyclohexane or paraffins such as mineral oil. aliphatic hydrocarbons such as distillates; alcohols such as butyl or glycols and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; highly polar solvents such as trimethylformamide and There is trimethyl sulfoxide as well as water.

The term liquefied gas extender or carrier refers to liquids that are gases at normal temperature and pressure, such as butane, propane, nitrogen, and carbon dioxide in the case of aerosol propellants such as halogen-substituted hydrocarbons.

Suitable solid carriers include: kaolin,
There are mills of natural minerals such as clay, talc, chalk, quartz, attapultzite, montmorillonite or diatomaceous earth, and mills of synthetic minerals such as highly dispersed silicic acid, alumina and silicates.

Suitable solid carriers for the granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, ceviolite and dolomite; as well as inorganic and organic! Coarse synthetic granules; organic materials such as sawdust, palm grain, corncob and tobacco stalk granules.

Suitable emulsifiers and/or foaming agents include: for example polyoxyethylene-aliphatic esters, polyoxyethylene-aliphatic alcohol ethers such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfones. There are nonionic and anionic emulsifiers such as acid salts as well as albumin hydrolysis products.

Suitable dispersants include, for example, trigenin-sulphite waste liquor and methylcellulose.

Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in powdered, granular or latex form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phosphors such as cephalin and lecithin, and synthetic phospholipids are also in the formulation. It can be used for

Other possible additives are mineral and vegetable oils.

Inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and colorants such as metal 7 talocyanine dyes, may also contain trace amounts of nutrients such as iron, manganese, boron, copper, cobalt. , molybdenum and zinc salts can also be used.

The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 05 to 90%.

The active compounds according to the invention may be used in combination with other active compounds, such as insecticides, poison baits, sterilizers,
It can be present as a mixture with acaricides, nematicides, fungicides, fungicides, growth regulator substances or herbicides.

Examples of insecticides include phosphoric acid esters, carbamic acid esters, and carboxyl esters. Includes chlorinated hydrocarbons, phenylureas, and substances produced by microorganisms.

The active compounds according to the invention may furthermore be used as synergistic agents in their commercially available formulations and in the use forms prepared from them.
agent).

A synergist is a compound that enhances the action of the active compound, but it is not necessary that the added synergist itself has activity.

Active compound storage in usage forms prepared from commercially available formulations (7
The amounts can vary within wide ranges. The active compound concentration of the use forms is from 0.0000001 to 95% by weight, preferably from o, o o o i to 1% by weight.

The compounds are used in a conventional manner appropriate to the mode of use.

When used against sanitary pests and stored product pests, the active compounds are distinguished by an excellent residual action on wood and clay and good stability against alkalis on lime-treated substrates.

The active compounds which can be used according to the invention are also suitable for the control of insects, ticks, non-Ixodes mites etc. in livestock husbandry and in the field of animal breeding, with good results, e.g. Increased weight gain, more attractive animal hides, more attractive animal hides, etc. can be achieved by controlling pests.

The active compounds according to the invention can be used, for example, in tablets, capsules,
By oral administration in the form of potables and granules; by dermal administration, e.g. in the form of dips, sprays, pours, rubs, and sprinkles; and parenteral administration, e.g. in the form of injections. Furthermore, “fees-throughha+ethod” 1
It is used by techniques known in the art, such as Koyoru. In addition, it can also be used in the form of molded products (neck collar or ear tag).
It is a Ding f version.

The biological activity of the compounds according to the invention may be illustrated with reference to the following examples.

Made by lino dragon - example χ standard ro 12 C.F.

5-7mi/-4-dichlorofluoromethylmercapto-
1-(2,6-fuchloro-4-trifluoromethylphenyl)-pyrazole15. (0,035 mol) is dissolved in a mixture of 100 ml of glacial acetic acid and 85% strength phosphorus P&3511 and 2°91? of sodium nitrite. A solution of (O, 042 mol) dissolved in 22 so 1 96% strength sulfuric acid is
Add at °C. This compound was stirred at 0°C for 1 hour,
50 ml of 50% strength sub-north phosphoric acid are then added directly at this temperature. After the addition is complete, the mixture is heated to O~
Stir at 10°C for 3 hours and then extract with 200a+l of methylene chloride. The phases are separated, washed with a solution of sodium bicarbonate and sodium chloride and dried over magnesium sulfate. The solvent is evaporated in vacuo. 14 when removed
．． A yellow oil of 28 is obtained, which is purified by column chromatography on silica gel and methylene chloride as fluid phase.

M Point 5 B'C 4-dichlorofluoromethanesulfenyl-1-(2+6-fuchloro-4-trifluoromethylphenyl)pyrazole 5.2 g (36% of the filled ml)
) is obtained.

1) [Mori-5-amino-1-(2,6-fuchloro-4-triple-omethyl)-pyrazole log (o, o 34 mol)
is dissolved in 50TO+ glacial acetic acid, and 6.1 g (O, 036 mol) of dichlorofluoromethanesulfenyl chloride is fully added at room temperature. The temperature rises to about 40°C. The reaction mixture is stirred for 2 hours and then introduced into a mixture of 200+++ l of water and 50 ml of methylene chloride. The organic phase is separated and the aqueous phase is extracted twice with 1 portion of methylene chloride. The combined organic phases are washed successively with sodium bicarbonate solution and sodium chloride solution, dried over magnesium sulfate "I:" and concentrated in vacuo.

5-Amino-4- with melting point 100'C to 103'C
Dichlorofluoromethanesulfenyl-1-(2゜6-
13.6 g (94% of theory) of dichloro-4-trifluoromethylphenyl)-pyrazole are obtained.

24.5 g (O, 1 mol) of 2.6-cyclo-4-trifluoromethylphenylhydrazine was mixed with 20 g of disodium ethylenecyaminetetraacetate (Tytribrex).
Titriplex)lli)2 (25 ml (27,6E+10.3 mol) of 2-chloroacrylonitrile is fully added to 1 to 8 in 150 ml of methanol at reflux temperature. After the addition is complete, this mixture is heated at reflux for a further 8 hours, then 9 ml (0, 16 mol) of 96% strength sulfuric acid are added in full and the mixture is heated at reflux for a further 6 hours.

The reaction mixture was cooled and 33.5 ml of anhydrous sodium carbonate was added.
g (O, 3 mol) is added. After 4 hours, the solvent is removed in vacuo, the residue is taken up in 500 ml of water, and the mixture is stirred at room temperature for 10 hours. The separated precipitate is filtered off, washed with water and dried in vacuo at 50'.

28.5 g (96% of theory) of 5-amiz-1-(2°6-dichloro-4-trifluoromethylphenyl)-pyrazole with melting point 10:(~105'C) are obtained.

KA appendix 1 5-7 minnow 4-dichlorofluoromethylmercapto
Dissolve 18.0 g (O, 046 mol) of 1-(2,4,6-)lifluorophenyl)-pyrazole in 60 ml of bromoform. and nitrous 11's31 chill 13.9g (
O, 135 mol) is added at room temperature. During this step the temperature rises to 40-50°C. Subsequently, the reaction mixture was stirred for 4 hours, diluted with 200 ml of methylene chloride, and
Wash successively with sodium bicarbonate solution, sodium thiosulfate solution and sodium chloride solution. The organic phase is dried over magnesium sulphate and the solvent is removed in vacuo. 5-bromo-4-dichlorofluoromethanesulfenyl-1-(2,4,6-)lichlorophenyl)-pyrazole 19, Og (FlmM
91%) is obtained.

Proboscis-Q-u 5-7 Minnow 1-(2,4,6-Dolichlorophenyl)
-Pyrazole 3. Og (O, 114 mol) and 10 ml (O, 125 mol) of anhydrous birinone in 15(,)lIll
of methylene chloride, and dichlorofluoromethanesulfenyl chloride 12. C) 101 (O, 12 mol) is added at 0°C to 5'C and the mixture is stirred for 30 minutes. For post-treatment, add 100 ml of methylene chloride,
The mixture is washed successively with dilute hydrochloric acid, water, sodium carbonate solution and sodium chloride solution, dried over magnesium sulfate and the solvent is removed in vacuo.

5-amino-4-dichlorol:+fluoromethanesulfenyl-1(2+4.6-
44.5 g (theoretical amount: 98.7 g) of )-lichlorophenyl)-pyrazole are obtained.

Shaku-LfL 4-dichlorofluoromethanesulfenyl-1-(2,
6-dichloro-4-) +7 fluoromethylphenyl)-pyrazole 2.1 g (O,005 mol)
90% strength TI-chlorobenzoic acid 1,2. (O,007 mol) at about 10°C
Add with The temperature was raised to 20°C over 2 hours, and then
This mixture is worked up as follows. The precipitated chlorobenzoic acid is filtered off and washed with a small amount of methylene chloride. The combined organic phases are washed with sodium bicarbonate solution, sodium thiosulfate solution and again of sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo.

1.9 g of 4-dichlorofluoromethanesulfenyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole (87% of the Fti stoichiometric amount) with a melting point of 144°C.
) is obtained.

The following 1-7 lylvirazoles of general formula (1) are obtained in a corresponding manner according to the general description of the preparation.

・1 1 ~ ~ − − ~ □ -Tough -- -C (J
CJ oko!
:e =:l:
! Size Ll”)
CoH+
■～ ('J
() ()11N 0 0
C10■+1? Chlotho-+-1+m+-1e-1111 1''~
゛〜0 − −
~ 0=ω
ω Co
ro 0 - ~
Zeng (to)
■ So So So ON −〇
~Q ω
B
ωO Loto ■
■Zeng 0li
ω C
Sharp 0 -
four-inch
−Noi
I0 0
0 C'J
0ω ω
ω ω
SonoOcO+++
of h of
j's 10
C%J%
cQOro ~
CO ■ TOI"-1++1%-TOQ ~ --~
00-C%J (a)
! ri ■ ■
■ ■Φ
0 0
~ 0 Roku
Co= co+++ (1)
■ [F]
of 40
〇＝
=1 Masashi: The indicated compound was used as a base in the following usage examples.

lohexyl-5-[N, N-(tumethyl)-carbamyloxy 1-3-methylthiomethylpyrazole (DE-
O3 (West German Open Mei #i?) ptS2.839.27
0) 0hexyl-5-[N,N-(dimethyl)-caroxy]-3-methylsulfinylbilacy O3 (West German Open Specification) @2,839.270) O 1-cyclohexyl- 5-[N,N-(trimethyl)-
Rubamyloxy 1-3-methylsulfonylmethylpyrazole (DE-O3 (West German Open Mei 1lII) No. 2,83
9,270) χ1M-Tomo7 Aedon Larva Test Solvent Near Part by Weight of Dimethylformamide Emulsifier: 1 Part by Weight of Furkylaryl Polyglycol Ether Active Compound To make a suitable formulation, 1 part by weight of mixing the active compound with the above amount of solvent and the above amount of emulsifier;
Dilute to the desired concentration with this thick floating liquid water.

Cabbage (Bra3Sica oleracea)
The leaves of mustard beetle (P L + aedon coc
hleriae) on wet leaves.

After a certain period of time, the mortality rate is determined in %. 100% means that all larvae died, 0% means that no larvae died.

In this test, for example, the compound of the Preparation Example below shows superior activity compared to the prior art.

Manufacturing example: 1.5.7.11.14,1 G, 4,2
8゜12.18.17, 40, 27.13, 39.37
, 10° 36.29.2, 19, 34.20.35 and 46 people (Ni primary damage insect) 7 Aedon larva test Δ (known) B (known) I C (known) CF, (14) Br (29) Two-spotted spider mite test (resistance) To prepare a suitable formulation of dimethylformamide emulsifier = 1 part by weight of furkylaryl polyglycol ether active compound, 1 part by weight of solvent: of the active compound with the above amount of solvent and the above amount of emulsifier,
This concentrate is diluted with water to the desired concentration.

Two-spotted spider mite or two-spotted spider mite at all stages of growth
E (Tetravychus urticae)
Seedlings of P. us vulgaris are treated by immersion in an active compound formulation of the desired concentration.

After a certain period of time, the mortality rate is determined in %. 100% means that all spider mites were killed; 0% means that no spider mites were killed.

In this test, for example, the compound of Example 9i below shows superior activity compared to the prior art.

Examples: 1.5, 14, 38, 2, 34, 10.20 and 36 people - Σ (Plant damaging insect) Two-spotted spider mite test^ (known) B (known) C (known) CF, (1) Limits Concentration test/soil insect test Insect: Pborbia anLi
aqua) larvae (in soil) Solvent: 3 parts 77 tons emulsifier = 1 part by weight furkylaryl polyglycol ether To make a suitable formulation, add 1 part by weight of the active compound. Mix with the above amount of solvent, add the above amount of emulsifier, and this t! Dilute the jk thick liquid to the desired concentration of floating liquid.

This active compound formulation is intimately mixed with the soil.

The active compound concentration in the formulation is of no practical importance (pp.
Only the weight of active compound per unit volume of soil, expressed in ugly (= mg/') liter), is decisive. Fill the pot with this soil and leave the pot at room temperature.

After 24 hours, the test animals are placed in the treated soil and after a further 2 to 7 days, the effectiveness of the active compound is determined by counting the dead and live test insects. The effectiveness is 100% if all the test insects are defeated and dead, and 0% if exactly the same number of test insects as in the untreated Jl control are still alive.

In this test, for example, the compounds of the Preparation Examples below show a better effect compared to the prior art.

Examples: 1, 14 and 16 Human-Con Soil Insect Black fly larvae in soil ^ (known) B (known) C (known) CF3 (llj) Tue 1 [- LT,,. Test (Diptera) Test animal: Musca dovestic
u) (Resistance) Number of test animals: 25 Seven tons of solvent 2 parts by weight of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired lower concentration.

Pipette 2.5 ml of this active compound solution and
Place in a veterinary dish. The bottom of this bedding dish has a diameter of approximately 9 mm.
5 The circular filter paper of e+a is the container. The bed dish is left uncovered until the solvent has completely evaporated.The amount of active compound per filter paper 1+I3 varies depending on the concentration of the active compound solution used. Then, place the two test animals in this bedding dish, and cover the bedding dish with a gamma-filled lid.

Continuously check the condition of the test animals. Measure the time required for 100% killing.

In this test, for example, 7 examples in which the compounds of the following preparation examples show better action compared to the prior art: 1, 8
．． 14 and 16 L digastric L D ,. . -Test Diptera (Housefly) 8 (Public) B (Public) C (Public) CF, (14) CF, (16) It has been a long time since I learned this lesson, (21) CF, (45) CF, (25) CF, (48) W-locus LT+oe test Test animal: S. 1tophilus
granarius) Number of test animals: 25 Seven tons of solvent 2 parts by weight of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired concentration.

Pipette 2 S ml of this active compound solution into a Petri dish. The bottom of this bird dish has a diameter of approximately 9 mm.
, 5 am circular tF paper is the container. The bedding dish is left uncovered until the solvent has completely evaporated.The amount of active compound per 3 sheets of F paper varies depending on the concentration of the active compound solution used. Then, the above number of test animals are placed in this petri dish, and the petri dish is covered with a glass lid.

Check the condition of the test animals 3 days after the start of the experiment. The mortality rate is measured in %. 100% means that all test animals died; 0% means that no test animals died.

In this test, for example, the compounds of the Preparation Examples below exhibit a better effect compared to the prior art.

Apex example: 1.7, 8, 11. 14, 16, 46, 79° 83tJ (LD once at /102... - Test weevil also ^ (known) B (known) C (known) Example F LT + oo test Test animals: Roif 7aea Maderae Number of test animals: 25 Solvent Nia Seven tons 2 parts by weight of the active compound are dissolved in 1000 parts by volume of solvent.The solution thus obtained is further diluted with the desired solvent. dilute to a concentration of

Pipette 2.5 ml of this active compound solution into a vetri dish. The bottom of this bird dish has a diameter of approximately 9.5 cm.
Contains circular filter paper. The Petri dish is left uncovered until the solvent has completely evaporated.The amount of active compound per filter paper varies depending on the concentration of the active compound solution used. Then, the above number of test animals are placed in this bedding dish, and the bedding dish is covered with an fft lid.

Check the condition of the test animals 3a after the start of the test. The mortality rate is measured in %. 100% means that all of the test animals died, and 0% means that none of the test animals died.

In this test, for example, the compounds of the Preparation Examples below show a better effect compared to the prior art.

Examples: 1, 8, 14, 46, 79, 83 and 102
゜ [LD,. . - Tests with resistant larvae of the Lueilia cuprina (OP-resistant Gundeiwindei variety) Q O,20B (known) Q O,20C (known) ) Milk (1:3 parts by weight of ethylene glycol monomethyl ether 35 parts by weight of 7-nylphenol polyglycol ether) To make a suitable formulation of the active compound, 3 parts by weight of the active compound are mixed with 7 parts by weight of 11 parts of the above emulsifier mixture. and the concentrate thus obtained is diluted with water to the desired concentration.

Approximately 20 resistant fly larvae were mixed with approximately 10m3 of horse meat and 0.5mj! into a test tube containing the above active compound formulation. After 24 hours, the mortality rate is determined.

In this test, for example, the compounds of the Preparation Examples below show a better effect compared to the prior art.

Examples 1, 8 and 14 - Open Stomoxys calcit - Larval Test OP - Resistant born winddi variety Example H Parasitic sand fly (S tomoxys calcit
Testing with adult insects of A. rans) Solvent: Cremophor To prepare a suitable formulation of the active compound, the active substance in question is mixed with the abovementioned solvent in a quantitative ratio of 1:2, thus obtained. Dilute the concentrate with water to the desired concentration.

10 Stable Flies (S tomoxys calei)
trans) adults are introduced one day before the start of the test into a vetri dish containing a sandwich impregnated with 1 mj2 of the active compound formulation to be tested. After 3 hours, the degree of mortality is determined in %. 100% means all the flies are dead.
0% means that no flies died.

In this test, for example, the compounds of the Preparation Examples below exhibit a better effect compared to the prior art.

Examples: 1 and 7. .

L Test on Stable Flies EXAMPLE I LT Test Animal: German Cockroach Solvent Nia 2 parts by weight of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired concentration.

This amount of active compound fi2,5mj! Pipette the
Place in a veterinary dish. The bottom of this bedding dish has a diameter of approximately 9mm. S
The ew one has paper in it. The bedding dish was left uncovered until the solvent had completely evaporated.
The amount of active compound per 13 varies depending on the concentration of the active compound solution used. Approximately 10 test animals are then placed in the bedding dish, and the bedding dish is covered with a glass lid.

Check the condition of the test animals 3 days after the start of the experiment. The mortality rate is measured in %.

In this test, for example, the compounds of the examples below showed up to 0.
It showed 100% mortality at a concentration of 2%.

Examples: 18.22, 21.2, 3, 45, 25, 46, 48,
50°55.62, 66.71, 73, 12, 4, 74
,27°79.82,83,34,30,85,88,
95,97゜99.101,102,80,96゜[LD,... - Test German cockroach active compound Active compound Killing rate concentration (
Solution (%) 1---□-No.------ SC, 0,002100

Claims (1)

[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, R^1 represents hydrogen, alkyl, or halogenoalkyl, and R^2 represents alkyl, halogenoalkyl, or any of represents optionally substituted aralkyl or aryl; R^3 represents hydrogen or halogen; Ar represents optionally substituted phenyl or pyridyl; n is a number of 0, 1 or 2; 1-arylpyrazole representing. 2. R^1 represents hydrogen or has 1 to 4 carbon atoms and, where appropriate, 1 to 9 identical or different halogen atoms, in each case linear; also represents optionally branched alkyl or halogenoalkyl, R^2 having in each case from 1 to 8 carbon atoms and, where appropriate, from 1 to 17 identical or different halogen atoms; , in each case represents alkyl or halogenoalkyl, which may be straight-chain or branched, or, as appropriate, having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety; have,
and phenylalkyl or phenyl, which may be mono- or polysubstituted in each case with the same or different substituents, in which the possible substituents on the phenyl are in each case: halogen, cyano, nitro and in each case 1 to 4 carbon atoms and optionally 1 to 4 carbon atoms in each alkyl moiety.
Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, halogenoalkoxy, halogeno, having from 9 identical or different halogen atoms, in each case linear or branched Represents alkylthio, halogenoalkylsulfinyl and halogenoalkylsulfonyl, R^3 represents hydrogen, fluorine, chlorine, bromine or iodine, and Ar is mono- or polysubstituted with the same or different substituents. There are also phenyl, 2-pyridyl,
3-pyridyl or 4-pyridyl, in each case with possible substituents; cyano, nitro, halogen, in each case with 1 to 4 carbon atoms, in each case straight chain alkyl, alkoxy and alkoxycarbonyl, which may be branched or branched, and in each case from 1 to 4 carbon atoms and from 1 to 9
halogenoalkyl or halogenoalkoxy, in each case linear or branched, having identical or different halogen atoms, and the group -S(O)_m-R^4 (this In the formula, R^4 represents amino, or in each case is alkyl, alkylamino, dialkylamino or halogenoalkyl, which may be linear or branched; Each alkyl moiety has 1 to 4 carbon atoms, and in the case of halogenoalkyl, it has 1 to 9 same or different halogen atoms, and m is a number of 0, 1 or 2. The formula ( I
) 1-arylpyrazole. 3. R^1 is hydrogen, methyl, ethyl, n- or i-
represents propyl or trifluoromethyl, R^2 is methyl, ethyl, n- or i-propyl,
n-, i-, s- or t-butyl, n- or i
-pentyl, n- or i-hexyl, chloromethyl, difluoromethyl, difluorochloromethyl, fluorodichloromethyl, trifluoromethyl, pentafluoroethyl, pentachloroethyl, fluorotetrachloroethyl, difluorotrichloroethyl, trifluorodichloroethyl, tetra phenyl, which represents fluorochloroethyl, heptafluoropropyl, chloroethyl, bromoethyl, chloropropyl or bromopropyl, or which may be mono-, di- or trisubstituted in each case by the same or different substituents; benzyl or phenethyl, and the possible substituents on phenyl are: fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, trifluoromethyl, methylsulfinyl, methylsulfonyl, trifluoromethoxy, tri represents fluoromethylthio, trifluorothimersulfinyl or trifluoromethylsulfonyl, R^3 represents hydrogen, fluorine, chlorine or bromine, and Ar is 1, 2, 3, 4 with the same or different substituents; or 2-pyridyl or 4-, which may be mono-, di-, tri- or tetra-substituted, in each case by the same or different substituents; represents pyridyl, in each case with possible substitution on phenyl or pyridyl, cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and i-propyl,
n-, i-, s- and t-butyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl ,
Tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, difluorodichloroethyl, trifluorodichloroethyl, pentachloroethyl, trifluoromethoxy, trichloromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, chloromethoxy, dichloromethoxy, difluoromethoxy, Pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, trifluoroethoxy, difluorodichloroethoxy, trifluorodichloroethoxy, pentachloroethoxy and the group -S(O)_m-R^4 (in this formula R^4 is amino , methylamino, ethylamino, dimethylamino, diethylamino, fluorodichloromethyl, difluorochloromethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoromethyl, methyl or ethyl, m represents the number of 0, 1 or 2 ), and n represents the number 0, 1 or 2.
) 1-arylpyrazole. 4.Formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) In the formula, R^1 represents hydrogen, alkyl, or halogenoalkyl, and R^2 is alkyl, halogenoalkyl, or substituted in any case. 5-Amino-1-arylpyrazole is an inorganic aralkyl or aryl, Ar is phenyl or pyridyl, which may be substituted, and n is a number of 0, 1 or 2. General formula ▲Mathematical formula characterized by reacting with a nitrate or an organic nitrite ester in the presence of a reaction aid, optionally in the presence of a hydrohalic acid, and optionally in the presence of a diluent , chemical formulas, tables, etc. ▼ (I) In the formula, R^1 and R^2 have the above meanings, R^3 represents hydrogen or halogen, and Ar and n have the above meanings. - A method for producing an arylpyrazole. 5. A pest control agent containing at least one 1-arylpyrazole of formula (I). 6. Insecticides and acaricides containing at least one 1-arylpyrazole of formula (I). 7. Insects and/or arachnids and/or the 1-arylpyrazole of formula (I) is applied to insects and/or arachnids and/or nematodes and/or their environment. How to control nematodes. 8. Use of 1-arylpyrazole of formula (I) for controlling insects and/or arachnids and/or nematodes. 9. A method for producing a pest control agent, which comprises mixing 1-arylpyrazole of formula (I) with an extender and/or a surfactant.